EP2563148A1 - Composition in the form of liquid for maintenance of contact lenses and medical materials - Google Patents
Composition in the form of liquid for maintenance of contact lenses and medical materialsInfo
- Publication number
- EP2563148A1 EP2563148A1 EP11727815A EP11727815A EP2563148A1 EP 2563148 A1 EP2563148 A1 EP 2563148A1 EP 11727815 A EP11727815 A EP 11727815A EP 11727815 A EP11727815 A EP 11727815A EP 2563148 A1 EP2563148 A1 EP 2563148A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- composition according
- hydrogen peroxide
- solution
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 239000007788 liquid Substances 0.000 title claims abstract description 6
- 238000012423 maintenance Methods 0.000 title description 4
- 239000012567 medical material Substances 0.000 title description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 36
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 78
- 239000000243 solution Substances 0.000 claims description 37
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 28
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 23
- 235000005493 rutin Nutrition 0.000 claims description 23
- 229960004555 rutoside Drugs 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229960005070 ascorbic acid Drugs 0.000 claims description 14
- 235000010323 ascorbic acid Nutrition 0.000 claims description 14
- 239000011668 ascorbic acid Substances 0.000 claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims description 10
- 239000004408 titanium dioxide Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 5
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 claims description 4
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 4
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000031700 light absorption Effects 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 2
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 claims description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims description 2
- XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 claims description 2
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 claims description 2
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 2
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 claims description 2
- 229940074391 gallic acid Drugs 0.000 claims description 2
- 235000004515 gallic acid Nutrition 0.000 claims description 2
- 229960004502 levodopa Drugs 0.000 claims description 2
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 claims description 2
- 229940079877 pyrogallol Drugs 0.000 claims description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 claims 1
- 230000002371 mycocidal effect Effects 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000011941 photocatalyst Substances 0.000 abstract description 12
- 102000004169 proteins and genes Human genes 0.000 description 20
- 108090000623 proteins and genes Proteins 0.000 description 20
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 19
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 19
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 19
- 239000000463 material Substances 0.000 description 18
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000001699 photocatalysis Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000003607 modifier Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 241000588724 Escherichia coli Species 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000002159 nanocrystal Substances 0.000 description 7
- 238000001782 photodegradation Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000003556 assay Methods 0.000 description 6
- 238000000502 dialysis Methods 0.000 description 6
- 238000001962 electrophoresis Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101100342332 Mus musculus Klf16 gene Proteins 0.000 description 4
- 230000032900 absorption of visible light Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 4
- 230000035899 viability Effects 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- GVXPWRLSQCRZHU-UHFFFAOYSA-N n,n'-bis(3-methylphenyl)methanediimine Chemical compound CC1=CC=CC(N=C=NC=2C=C(C)C=CC=2)=C1 GVXPWRLSQCRZHU-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000001332 colony forming effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 2
- 238000007146 photocatalysis Methods 0.000 description 2
- 150000003021 phthalic acid derivatives Chemical group 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000017854 proteolysis Effects 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KFZNPGQYVZZSNV-UHFFFAOYSA-M azure B Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(NC)=CC=C3N=C21 KFZNPGQYVZZSNV-UHFFFAOYSA-M 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- -1 hydrogen peroxide Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
Definitions
- the subject of the present invention is a composition, especially in the form of a liquid for an external use, for treatment and maintenance of contact lenses, containing nanocrystalline photocatalyst active upon visible light illumination and eventually hydrogen peroxide.
- the goal of the present invention is to deliver a composition for the production of solutions exhibiting sterilizing properties upon irradiation with visible light and therefore suitable for maintenance of various materials, especially those requiring physiological use, as contact lenses, medical materials (catheters, bandages, syringes, etc.).
- the subject of the present invention is the composition containing titanium dioxide Ti0 2 modified on its surface with an organic compound selected from a group encompassing: i. a compound described by the general formula:
- R denotes -H, -NH 2 , -NH 3 + or -S0 3 M, in which M denotes H + , K + , Na + , Li + , NH 4 + ,
- the composition according to the invention is in the form of liquid containing a colloidal solution in which the dispersed phase is composed of the surface modified nanoparticles of titanium dioxide characterized by the particle size lower than 100 nm, while the aqueous solution of hydrogen peroxide plays the role of the dispersion medium.
- the composition according to the present invention exhibits visible light absorption as well as photocatalytic activity in a wavelength range ( ⁇ ) no smaller than ca. 400 nm (the arbitrary threshold between ultraviolet and visible light) to about 600 nm, preferably to ca. 700 nm, as well as absorption of ultraviolet light ( ⁇ ⁇ 400 nm).
- ⁇ wavelength range
- the organic compound is a compound selected from the group encompassing: phthalic acid, 4-sulfophthalic acid, 4-amino-2-hydroxybenzoic acid, 3- hydroxy-2-naphthylic acid, salicylic acid, 6-hydroxysalicylic acid, 5-hydroxysalicylic acid, 5- sulfosalicylic acid, 3,5-dinitrosalicylic acid, disodium salt of l,4-dihydroxy-l,3- benzenedisulfonic acid, gallic acid, pyrogallol, 2,3-naphthalenediol, 4-methylcatechol, 3,5-di- iert-butylcatechol, p-nitrocatechol, 3,4-dihydroxy-L-phenylalanine (DOPA), rutin as well as ascorbic acid.
- DOPA 3,4-dihydroxy-L-phenylalanine
- the compound bound to the surface is a compound selected from the group encompassing: disodium salt of 4,5-dihydroxy-l,3-benzenedisulfonic acid, rutin and ascorbic acid.
- composition according to the invention contains additionally a buffer, preferably isotonic, stabilizing pH value within the acceptable pharmaceutical range.
- a buffer preferably isotonic, stabilizing pH value within the acceptable pharmaceutical range.
- the composition according to the invention contains the surface modified nanocrystalline titanium dioxide within the concentration range of 0.02 to 1 g dm and hydrogen peroxide, preferably in the concentration range of 0.001 to 0.1 g dm .
- composition according to the invention can additionally contain pharmaceutical carriers and excipients.
- carriers and excipients the known carriers and excipients used in pharmacy, that are compatible with the active substance, can be applied.
- the modified titanium dioxide characterized by particle size not exceeding 100 nm constitutes stable colloidal systems in solution of PBS buffer, retaining its photocatalytic activity.
- the composition according to the invention constitutes a clear, transparent aqueous solution, containing hydrogen peroxide and nanocrystalline titanium dioxide, the surface of which has been modified with rutin, as the active substances, together with NaCl and phosphate buffer.
- the composition according to the invention or the colloidal solution of titanium dioxide nanoparticles is prepared as a concentrate, preferably containing 40-50 times higher concentration of titanium dioxide as compared to its final concentration in the composition.
- the concentrate should be diluted with water, preferably with aqueous buffer solution, isotonic aqueous solution, hydrogen peroxide and eventually other additives to the final concentration of all ingredients.
- the composition according to the invention is used to the external use as a contact lens cleaning solution.
- the composition can be used in the production of a preparation for sterilisation or disinfection, preferably in the production of a photosterilising, photobacteriocidal, photomycocidal, or photocatalytic preparation particularly designed for use in one of the following areas: cosmetology, dermatology, ophthalmology, laryngology, urology, gynaecology, rheumatology, oncology, surgery, veterinary medicine, dentistry, in particular for the sterilization of surfaces and glass or plastic elements, particularly contact lenses, medical catheters, glass and/or plastic conduits as well as other surfaces, the sterilization of which is desirable and/or required.
- composition according to the present invention exhibits photocatalytic activity upon irradiation with visible light ( ⁇ > 400 nm; photocatalysis is the result of the absorption of visible light by the titanium surface complex of the charge-transfer type), as well as ultraviolet light ( ⁇ ⁇ 400 nm; photocatalysis is the result of the absorption of ultraviolet light by the titanium surface complex of the charge-transfer type or directly by titanium dioxide).
- the irradiation generates so-called reactive oxygen species (OH * , 0 2 " ⁇ , H 2 0 2 , l 2 ).
- Fig. 1 shows UV-vis absorption spectra of a colloidal solution of Ti0 2 nanocrystals modified respectively with compound K-1 (Table 2) (a), ascorbic acid (b) and rutin (c) (each concentration: 0.4 g dm );
- Fig. 2 shows a TEM image recorded for the material K-l @Ti0 2 ;
- Fig. 1 shows UV-vis absorption spectra of a colloidal solution of Ti0 2 nanocrystals modified respectively with compound K-1 (Table 2) (a), ascorbic acid (b) and rutin (c) (each concentration: 0.4 g dm );
- Fig. 2 shows a TEM image recorded for the material K-l @Ti0 2 ;
- Fig. 1 shows UV-vis absorption spectra of a colloidal solution of Ti0 2 nanocrystals modified respectively with compound K-1 (Table 2) (a), ascorbic acid (b) and rutin (c) (each concentration: 0.4
- E. coli viability tests in the presence of a colloidal solution of Ti0 2 nanocrystals modified with K-1 (grey) and in the absence of the photocatalyst (black) (a) during irradiation with light ⁇ > 420 nm and (b) E. coli viability test results in the same system in the dark, as well as E. coli viability tests in the presence of a colloidal solution of Ti0 2 nanocrystals modified with ascorbic acid (squares) and in the absence of the photocatalyst (triangles) (c) upon irradiation with light ⁇ > 420 nm and (d) E. coli viability test results in the same system in the dark.
- Figure 5 shows the results described in the Example 5 of the comparative tests of photoactivity of the composition according to the present invention, or its components, in the process of proteins oxidation.
- Figure 6 shows the results described in the Example 6 of the comparative tests of photoactivity of the composition according to the present invention, or its components, in the process of bacteria inactivation.
- Figure 7 presents the results of azure B photooxidation proving the unexpected synergy between activity of the photocatalyst and hydrogen peroxide.
- Example 1 Production of a nanocrystalline photocatalyst active in visible light
- the initial substrate for the synthesis of the materials in question is an unmodified nanocrystalline Ti0 2 , which may be produced according to various known procedures. One of them is proposed by Wang et al. (J. Phys. Chem. B, 2000, 104, 93-104). Particles of titanium dioxide Ti0 2 smaller than 100 nm (estimated using imaging with a transmission electron microscope) is modified on its surface directly via chemisorption of an organic compound selected from the group according to the present invention with the formation of charge- transfer complexes. Photoinduced electron transfer occurs between the organic compound molecule and the semiconductor particle.
- a photoactive colloid according to the present invention is characterized by a high degree of dispersion and occurs in the form of a suspension or emulsion.
- an appropriate buffer i.e. SSC or PBS
- Ti0 2 nanocrystals modified with ascorbic acid or another organic compound according to the present invention may then be subjected to further modifications consisting of conjugation with a molecule increasing the specificity of their activity (i.e. an antibody, peptide, biotin or vitamins).
- a molecule increasing the specificity of their activity i.e. an antibody, peptide, biotin or vitamins.
- UV-vis spectrum of the KA@Ti0 2 material is shown in Figure lb. Like other materials (stable in acidic solutions) KA@Ti0 2 shows absorption of visible light up to ca. 600-700 nm. UV-vis spectrum of the rutin @Ti0 2 solution is shown in Fig lc. The material shows absorption of visible light to a wavelength of 600 nm.
- Photodegradation tests were carried out with bovine serum albumin (as a model protein) upon visible light irradiation in the presence of nanocrystalline Ti0 2 modified by organic compound selected from the group according to the present invention.
- the protein concentration in solution was monitored using semi-quantitative method of polyacrylamide gel electrophoresis under denaturing conditions (SDS-PAGE).
- SDS-PAGE semi-quantitative method of polyacrylamide gel electrophoresis under denaturing conditions
- the reaction mixtures irrespective of the modification of nanocrystalline Ti0 2 , were prepared as follows: A solution of modified Ti0 2 (in an amount to yield a final concentration of 0.4 mg/ml in terms of Ti0 2 ) was mixed with bovine albumin (final concentration 0.4 mg/ml) and water to a final volume of 2 ml.
- Irradiation was performed using a high-pressure mercury lamp, HBO-500, as a light source and filters delivering light at a wavelength in the range 420-800 nm. Tests were performed in a quvette purged with a small stream of air during irradiation to ensure a constant oxygen level in solution. During the experiment, samples were taken and subjected to electrophoresis following denaturation in order to monitor the degree of albumin degradation. The electrophoresis was performed in a Laemmli system using a 10% separating gel and a 4% stacking gel. The results are shown in Fig. 3. Sample 0' corresponds to an image of 2 ⁇ g of protein.
- the photodegradation assays of protein have confirmed the high level of photocatalytic activity of K-l @Ti0 2 upon visible light irradiation.
- the compiled protein electrophoresis images show protein degradation over the exposure time in a sample containing the protein and modified titanium dioxide in water. In the spectral range of 400- 800 nm (Fig. 3a) one can observe a clear decrease of protein concentration during irradiation. In a narrower radiation ranges, 435-800 nm and 455-800 nm, the results are slightly poorer than the initial ones (Fig. 3b and 3c).
- Protein photodegradation assays have confirmed the high level of photocatalytic activity of KA@Ti0 2 upon visible light irradiation. During irradiation within the spectral ranges 400-800 nm and 420-800 nm (Fig. 3d and 3e, respectively) a clear decrease in protein concentration can be observed within several minutes.
- Protein photodegradation assays have confirmed the high level of photocatalytic activity of rutin @Ti0 2 upon visible light irradiation.
- the compiled protein electrophoresis images show protein degradation over the exposure time in a sample containing the protein and modified titanium dioxide in water. Both in the spectrum range 420-800 nm (Fig. 3f) and in a narrower range of radiation, 455-800 nm (Fig. 3g) one can observe clear decrease in protein concentration throughout the time of exposure.
- the assays of the ability of the new materials to photoinactivate microorganisms were performed on a model strain of Escherichia coli, and the absence of cytotoxicity in this material to this bacterial strain was demonstrated.
- the tests assaying the efficiency of the photoinactivation of microorganisms were performed thusly: A suspension of bacteria in water (ca. 10 6 CFU/ml determined spectrophoto metrically) was supplemented with a colloidal solution of nanocrystalline Ti0 2 modified with an organic compound selected from the group according to the present invention, to its final concentration of 0.4 mg/ml.
- the assays were performed under the same irradiation conditions as the protein photodegradation assays (2 ml samples, see above) using a cut-off filter ⁇ > 420 nm, aerating the sample during irradiation. Small samples were collected in order to evaluate the colony-forming potential of the examined strain. The colony formation ability was determined in dishes through the inoculation of 100 ⁇ aliquots of a serial dilution of the bacterial suspension onto minimal medium (DIFCO) and counting the colonies. The results are shown as cell survival fractions S/So.
- Example 5 Comparison of activity of the composition according to the invention and composition without the additives active towards proteins
- the activity of the mixture of the photocatalyst and hydrogen peroxide is considerably strengthened as compared to the separate use of the photocatalyst and hydrogen peroxide.
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Abstract
Description
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL391056A PL229207B1 (en) | 2010-04-26 | 2010-04-26 | Liquid composition for contact lens and medical materials care |
PCT/PL2011/050011 WO2011136672A1 (en) | 2010-04-26 | 2011-04-23 | Composition in the form of liquid for maintenance of contact lenses and medical materials |
Publications (2)
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EP2563148A1 true EP2563148A1 (en) | 2013-03-06 |
EP2563148B1 EP2563148B1 (en) | 2016-08-24 |
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EP11727815.0A Not-in-force EP2563148B1 (en) | 2010-04-26 | 2011-04-23 | Composition in the form of liquid for maintenance of contact lenses and medical materials |
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US (1) | US20130122073A1 (en) |
EP (1) | EP2563148B1 (en) |
JP (1) | JP5902672B2 (en) |
KR (1) | KR101841303B1 (en) |
AU (1) | AU2011245778A1 (en) |
BR (1) | BR112012027497B1 (en) |
CA (1) | CA2797491C (en) |
ES (1) | ES2601627T3 (en) |
MX (1) | MX340755B (en) |
PL (2) | PL229207B1 (en) |
RU (1) | RU2581827C2 (en) |
WO (1) | WO2011136672A1 (en) |
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ITMI20120171A1 (en) * | 2012-02-08 | 2013-08-09 | Alessio Gerardo Maugeri | PLANTS FOR NANOMATERIAL INCLUDING FLUIDS |
ITMI20120172A1 (en) * | 2012-02-08 | 2013-08-09 | Alessio Gerardo Maugeri | OPHTHALMIC AND NANOMATERIAL DEVICES |
PL229321B1 (en) * | 2012-07-23 | 2018-07-31 | Univ Jagiellonski | TiO2 photocatalytic coating on the surfaces of polymer, visible light activated, process for their preparation and the use thereof |
ITAR20130026A1 (en) * | 2013-07-16 | 2015-01-17 | A Chi Mo S R L | DISINFECTANT FOR WATER, IN PARTICULAR FOR THE WATER OF THE POOLS, AND ITS PRODUCTION METHOD. |
CN103439448B (en) * | 2013-07-25 | 2015-07-15 | 闽南师范大学 | Method used for rapid separation and detection of organophosphorus pesticides in water |
SE2150715A1 (en) * | 2021-04-23 | 2022-10-24 | Aurena Laboratories Holding Ab | Transition metal oxide adducts for regulated generation of reactive oxygen species |
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JP2003093481A (en) * | 2001-09-25 | 2003-04-02 | Menicon Co Ltd | Sterilizing and disinfecting device for contact lens |
JP2005211545A (en) * | 2004-02-02 | 2005-08-11 | Toyota Central Res & Dev Lab Inc | Disinfection method and disinfectant solution for contact lens |
US20070078190A1 (en) * | 2005-09-30 | 2007-04-05 | Distefano Frank V | Use of 2,3-dihydroxynaphthalene-6-sulfonic acid salts as dispersants |
CN101028528A (en) * | 2006-02-27 | 2007-09-05 | 权力敏 | Biological light catalyst |
EP2059267B1 (en) * | 2006-08-16 | 2012-04-18 | Novartis AG | Temporal photo-bleaching of colored lens care solutions |
AT504151A1 (en) * | 2006-08-17 | 2008-03-15 | Alfred Konzett | MEDICINAL PRODUCT, USE OF A PHOTOREACTIVE AGENT FOR THE MANUFACTURE OF SUCH A MEDICAMENT AND TREATMENT AGENT FOR THE TREATMENT OF SURFACE MUSHROOMS, BACTERIA AND VIRUS DISEASES USING SUCH A MEDICAMENT |
WO2010098687A2 (en) * | 2009-02-26 | 2010-09-02 | Uniwersytet Jagielloński | Nanocrystalline photocatalytic colloid, a method of producing it and its use |
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2010
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2011
- 2011-04-23 PL PL11727815T patent/PL2563148T3/en unknown
- 2011-04-23 JP JP2013507905A patent/JP5902672B2/en not_active Expired - Fee Related
- 2011-04-23 BR BR112012027497-0A patent/BR112012027497B1/en not_active IP Right Cessation
- 2011-04-23 MX MX2012012532A patent/MX340755B/en active IP Right Grant
- 2011-04-23 RU RU2012145755/15A patent/RU2581827C2/en not_active IP Right Cessation
- 2011-04-23 WO PCT/PL2011/050011 patent/WO2011136672A1/en active Application Filing
- 2011-04-23 KR KR1020127029884A patent/KR101841303B1/en active IP Right Grant
- 2011-04-23 ES ES11727815.0T patent/ES2601627T3/en active Active
- 2011-04-23 CA CA2797491A patent/CA2797491C/en not_active Expired - Fee Related
- 2011-04-23 EP EP11727815.0A patent/EP2563148B1/en not_active Not-in-force
- 2011-04-23 AU AU2011245778A patent/AU2011245778A1/en not_active Abandoned
- 2011-04-23 US US13/643,484 patent/US20130122073A1/en not_active Abandoned
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Also Published As
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WO2011136672A1 (en) | 2011-11-03 |
ES2601627T3 (en) | 2017-02-15 |
MX2012012532A (en) | 2013-05-09 |
RU2012145755A (en) | 2014-06-10 |
AU2011245778A1 (en) | 2012-11-15 |
JP2013525426A (en) | 2013-06-20 |
PL229207B1 (en) | 2018-06-29 |
US20130122073A1 (en) | 2013-05-16 |
RU2581827C2 (en) | 2016-04-20 |
BR112012027497A2 (en) | 2018-08-07 |
EP2563148B1 (en) | 2016-08-24 |
JP5902672B2 (en) | 2016-04-13 |
PL2563148T3 (en) | 2017-02-28 |
MX340755B (en) | 2016-07-25 |
CA2797491C (en) | 2018-01-02 |
KR101841303B1 (en) | 2018-03-22 |
CA2797491A1 (en) | 2011-11-03 |
KR20130058691A (en) | 2013-06-04 |
BR112012027497B1 (en) | 2019-09-24 |
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